Dimethylcarbamoyl Chloride → tert-Butyl 6-cyano-2-pyridylmethylcarbamate

HRID 748284ノート

反応式

HRID 748284 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH+:8]([O-])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].C[Si]([C:21]#[N:22])(C)C.CN(C)C(Cl)=O>[N+](CC)([O-])=O>[C:21]([C:6]1[N:1]=[C:2]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:3]=[CH:4][CH:5]=1)#[N:22]

参加物

5

反応物 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 86596464tert-Butyl 2-pyridylmethylcarbamate N-oxide

生成物 1

HCID 22939432tert-Butyl 6-cyano-2-pyridylmethylcarbamate収率 58%

試薬・触媒・溶媒 1

HCID 6587Nitroethane溶媒

実験手順

tert-Butyl 2-pyridylmethylcarbamate N-oxide (3.0 g, 13.3 mmol) was dissolved in nitroethane (50 ml), and trimethylsilyl cyanide (2.8 g, 28.6 mmol) and N,N-dimethylcarbamoyl chloride (1.7 g, 16.2 mmol) were added thereto. The mixture was stirred at room temperature for 24 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-hexane (2:1, v/v) were collected, concentrated and recrystallized from hexane-ethyl acetate to give the titled compound (1.8 g, 58%) as white crystals.

後処理

  1. customThe solvent was evaporated
  2. washThe fractions eluted with ethyl acetate-hexane (2:1
  3. customv/v) were collected
  4. concentrationconcentrated
  5. customrecrystallized from hexane-ethyl acetate

出典と根拠

ORDレコード
ord-13c3cde350b843aeb5a8b8ba42d925ab
出典データセット
uspto-grants-2008_07
特許番号
US07399759B2

反応ノート

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